1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity

Inbal Lapidot; Amnon Albeck; Gary Gellerman; Shimon Shatzmiller; Flavio Grynszpan

doi:10.1007/s10989-015-9460-1

1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity

Inbal Lapidot, Amnon Albeck, Gary Gellerman, Shimon Shatzmiller, Flavio Grynszpan

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

We synthesized new broad spectrum antibacterial cationic peptidomimetics centered on a hydrophobic 1,4-dihydropyridine (1,4-DHP) scaffold. The synthesis involves the preparation of the scaffold in a three step Hantzsch reaction followed by simultaneous coupling of the 1,4-DHP scaffold to two dipeptides bearing cationic side chains. The synthesized peptidomimetics were found to have no measurable toxic hemolytic effect against mammalian red blood cells. The compounds were found to have antibacterial activity against Gram-(-) and Gram-(+) bacteria with MICs in the range of 35-100 μg/mL. These cationic antimicrobial peptidomimetics will lead to more effective antibacterial drug candidates based on a synthetically accessible scaffold.

Original language	English
Pages (from-to)	243-247
Number of pages	5
Journal	International Journal of Peptide Research and Therapeutics
Volume	21
Issue number	3
DOIs	https://doi.org/10.1007/s10989-015-9460-1
State	Published - 27 Sep 2015

Bibliographical note

Publisher Copyright:
© 2015 Springer Science+Business Media.

Funding

The authors thank Dr. Hugo Gottlieb from Bar-Ilan University for NMR experiments and helpful advice. We also thank Dr. Galina M. Zats for compounds 11 and 12 . This work was supported by the Authority for Research & Development of Ariel University.

Funders	Funder number
Authority for Research & Development of Ariel University

Keywords

1, 4-dihydropyridine scaffold
Anti-microbial
Broad spectrum anti-bacterial
Cationic peptides
Drug design
Peptidomimetics

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10.1007/s10989-015-9460-1

Cite this

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abstract = "We synthesized new broad spectrum antibacterial cationic peptidomimetics centered on a hydrophobic 1,4-dihydropyridine (1,4-DHP) scaffold. The synthesis involves the preparation of the scaffold in a three step Hantzsch reaction followed by simultaneous coupling of the 1,4-DHP scaffold to two dipeptides bearing cationic side chains. The synthesized peptidomimetics were found to have no measurable toxic hemolytic effect against mammalian red blood cells. The compounds were found to have antibacterial activity against Gram-(-) and Gram-(+) bacteria with MICs in the range of 35-100 μg/mL. These cationic antimicrobial peptidomimetics will lead to more effective antibacterial drug candidates based on a synthetically accessible scaffold.",

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AU - Grynszpan, Flavio

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1,4-Dihydropyridine Cationic Peptidomimetics with Antibacterial Activity

Abstract

Bibliographical note

Funding

Keywords

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